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The title compound, C21H14Cl2O, was prepared from biphenyl-4-carbaldehyde and 2,4-dichloro­acetophenone. Single crystals were obtained from acetone. The compound crystallizes with four mol­ecules in the asymmetric unit, all of which deviate significantly from planarity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006897/bt2258sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006897/bt2258Isup2.hkl
Contains datablock I

CCDC reference: 640270

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.050
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT230_ALERT_2_C Hirshfeld Test Diff for C72 - C73 .. 6.52 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

(2E)-3-(Biphenyl-4-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one top
Crystal data top
C21H14Cl2OZ = 8
Mr = 353.25F(000) = 1456
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6022 (6) ÅCell parameters from 160 reflections
b = 11.9149 (14) Åθ = 18.0–4.8°
c = 37.877 (4) ŵ = 0.39 mm1
α = 85.413 (8)°T = 296 K
β = 85.375 (6)°Block, light yellow
γ = 86.547 (7)°0.60 × 0.53 × 0.23 mm
V = 3403.7 (6) Å3
Data collection top
Bruker-Nonius KappaCCD
diffractometer
7410 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
φ and ω scansθmax = 25.0°, θmin = 4.5°
Absorption correction: numerical
(Herrendorf & Bärnighausen, 1997)
h = 98
Tmin = 0.810, Tmax = 0.911k = 1414
30533 measured reflectionsl = 4544
11578 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0268P)2 + 1.7147P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max = 0.002
S = 1.06Δρmax = 0.24 e Å3
11578 reflectionsΔρmin = 0.31 e Å3
866 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0043 (4)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4206 (4)0.7906 (2)0.50965 (7)0.0558 (7)
C20.4236 (4)0.6776 (3)0.50521 (8)0.0737 (9)
H20.39100.65180.48430.088*
C30.4760 (5)0.6035 (3)0.53241 (8)0.0810 (10)
H30.47860.52660.52950.097*
C40.5249 (4)0.6385 (2)0.56390 (7)0.0600 (7)
C50.5177 (3)0.7529 (2)0.56744 (7)0.0546 (7)
C60.4660 (3)0.8291 (2)0.54046 (8)0.0577 (7)
H60.46200.90610.54320.069*
C70.5847 (5)0.5489 (3)0.59108 (8)0.0761 (9)
C80.5221 (4)0.5573 (2)0.62831 (7)0.0649 (8)
H80.43430.61220.63390.078*
C90.5848 (4)0.4903 (2)0.65432 (7)0.0607 (7)
H90.67340.43690.64790.073*
C100.5303 (3)0.4911 (2)0.69195 (7)0.0488 (6)
C110.5759 (3)0.3998 (2)0.71504 (7)0.0571 (7)
H110.64530.33970.70630.069*
C120.5213 (3)0.3957 (2)0.75045 (7)0.0532 (7)
H120.55240.33220.76500.064*
C130.4207 (3)0.4837 (2)0.76514 (6)0.0428 (6)
C140.3791 (3)0.5765 (2)0.74204 (7)0.0494 (6)
H140.31400.63800.75100.059*
C150.4312 (3)0.5800 (2)0.70651 (7)0.0519 (7)
H150.39960.64330.69190.062*
C160.3596 (3)0.4771 (2)0.80328 (7)0.0445 (6)
C170.4362 (4)0.3994 (2)0.82755 (7)0.0587 (7)
H170.53180.35280.81980.070*
C180.3746 (4)0.3894 (3)0.86264 (8)0.0683 (8)
H180.42790.33600.87820.082*
C190.2357 (4)0.4573 (3)0.87494 (8)0.0669 (8)
H190.19280.44940.89860.080*
C200.1605 (4)0.5368 (3)0.85195 (8)0.0691 (8)
H200.06810.58480.86020.083*
C210.2206 (4)0.5463 (2)0.81658 (7)0.0580 (7)
H210.16680.60030.80130.070*
C220.0706 (4)0.2058 (3)0.49291 (7)0.0631 (8)
C230.0396 (5)0.3182 (3)0.49504 (9)0.0915 (11)
H230.00460.36410.47550.110*
C240.0608 (6)0.3631 (3)0.52659 (9)0.0974 (12)
H240.04000.44040.52800.117*
C250.1114 (4)0.2989 (3)0.55622 (7)0.0634 (8)
C260.1436 (3)0.1851 (2)0.55263 (7)0.0557 (7)
C270.1244 (3)0.1384 (3)0.52122 (7)0.0603 (7)
H270.14800.06160.51930.072*
C280.1308 (4)0.3600 (3)0.58857 (8)0.0746 (9)
C290.0702 (4)0.3106 (2)0.62357 (7)0.0614 (8)
H290.00830.24520.62510.074*
C300.1000 (4)0.3554 (2)0.65318 (7)0.0575 (7)
H300.16220.42080.65050.069*
C310.0473 (3)0.3151 (2)0.68940 (7)0.0479 (6)
C320.0680 (3)0.3813 (2)0.71707 (7)0.0551 (7)
H320.11860.45050.71200.066*
C330.0166 (3)0.3483 (2)0.75157 (7)0.0531 (7)
H330.03220.39570.76930.064*
C340.0584 (3)0.2456 (2)0.76077 (7)0.0445 (6)
C350.0760 (3)0.1775 (2)0.73299 (7)0.0508 (7)
H350.12310.10730.73810.061*
C360.0256 (3)0.2113 (2)0.69842 (7)0.0527 (7)
H360.04030.16400.68060.063*
C370.1182 (3)0.2114 (2)0.79803 (7)0.0476 (6)
C380.0477 (4)0.2564 (2)0.82621 (7)0.0596 (7)
H380.04230.30620.82160.072*
C390.1085 (5)0.2286 (3)0.86064 (8)0.0713 (9)
H390.05980.26000.87910.086*
C400.2405 (4)0.1547 (3)0.86819 (8)0.0715 (9)
H400.28180.13620.89160.086*
C410.3104 (4)0.1087 (3)0.84083 (9)0.0681 (8)
H410.39980.05850.84570.082*
C420.2497 (4)0.1359 (2)0.80610 (8)0.0584 (7)
H420.29770.10320.78780.070*
C430.3203 (4)0.4242 (3)0.97707 (7)0.0619 (8)
C440.2305 (4)0.5264 (3)0.97131 (7)0.0657 (8)
H440.11730.53890.98200.079*
C450.3089 (4)0.6099 (2)0.94970 (7)0.0586 (7)
H450.24850.67960.94600.070*
C460.4761 (4)0.5925 (2)0.93325 (7)0.0532 (7)
C470.5633 (4)0.4892 (3)0.94000 (8)0.0617 (8)
C480.4867 (5)0.4043 (2)0.96194 (8)0.0664 (8)
H480.54750.33510.96630.080*
C490.5488 (4)0.6882 (3)0.90946 (8)0.0587 (7)
C500.6233 (4)0.6666 (2)0.87348 (8)0.0619 (8)
H500.61020.59680.86490.074*
C510.7082 (4)0.7437 (2)0.85318 (7)0.0586 (7)
H510.72090.81070.86350.070*
C520.7848 (3)0.7393 (2)0.81700 (7)0.0499 (6)
C530.8732 (4)0.8304 (2)0.80128 (8)0.0578 (7)
H530.88760.89100.81460.069*
C540.9404 (3)0.8338 (2)0.76656 (8)0.0561 (7)
H540.99870.89680.75690.067*
C550.9238 (3)0.7457 (2)0.74545 (7)0.0473 (6)
C560.8366 (3)0.6528 (2)0.76146 (7)0.0532 (7)
H560.82330.59180.74820.064*
C570.7701 (3)0.6492 (2)0.79626 (7)0.0546 (7)
H570.71420.58550.80620.066*
C580.9912 (3)0.7523 (2)0.70761 (7)0.0514 (7)
C591.1162 (4)0.8286 (2)0.69462 (8)0.0628 (8)
H591.15960.87520.71010.075*
C601.1769 (4)0.8367 (3)0.65942 (9)0.0771 (9)
H601.25980.88900.65130.092*
C611.1166 (5)0.7685 (3)0.63628 (9)0.0815 (10)
H611.15860.77390.61250.098*
C620.9941 (5)0.6923 (3)0.64836 (9)0.0812 (10)
H620.95260.64560.63270.097*
C630.9317 (4)0.6843 (3)0.68368 (8)0.0667 (8)
H630.84810.63220.69150.080*
C640.1609 (5)1.0668 (3)0.96961 (8)0.0725 (9)
C650.2208 (5)0.9713 (3)0.95769 (9)0.0762 (9)
H650.32830.94360.96690.091*
C660.1193 (5)0.9177 (3)0.93207 (9)0.0711 (9)
H660.15820.85180.92450.085*
C670.0389 (4)0.9573 (2)0.91694 (8)0.0615 (8)
C680.0949 (4)1.0529 (3)0.92995 (9)0.0690 (8)
C690.0028 (5)1.1079 (3)0.95608 (9)0.0760 (9)
H690.03771.17210.96450.091*
C700.1314 (4)0.8929 (3)0.88800 (9)0.0701 (8)
C710.1991 (4)0.9530 (3)0.85476 (9)0.0674 (8)
H710.18311.03110.85190.081*
C720.2825 (4)0.8978 (3)0.82882 (9)0.0673 (8)
H720.30210.82070.83390.081*
C730.3476 (3)0.9409 (2)0.79357 (8)0.0575 (7)
C740.4375 (4)0.8669 (2)0.77100 (9)0.0653 (8)
H740.45540.79150.77900.078*
C750.5003 (4)0.9019 (2)0.73744 (9)0.0636 (8)
H750.55910.84960.72310.076*
C760.4790 (3)1.0133 (2)0.72409 (8)0.0548 (7)
C770.3869 (4)1.0873 (2)0.74668 (9)0.0614 (8)
H770.36821.16250.73860.074*
C780.3233 (4)1.0523 (2)0.78030 (9)0.0636 (8)
H780.26261.10420.79460.076*
C790.5512 (4)1.0518 (2)0.68816 (8)0.0584 (7)
C800.6949 (4)0.9939 (3)0.67133 (10)0.0701 (9)
H800.74460.92920.68280.084*
C810.7644 (5)1.0302 (3)0.63828 (11)0.0831 (10)
H810.86020.99000.62760.100*
C820.6946 (5)1.1248 (4)0.62088 (9)0.0832 (10)
H820.74211.14890.59840.100*
C830.5535 (5)1.1844 (3)0.63672 (10)0.0857 (10)
H830.50631.24970.62510.103*
C840.4824 (4)1.1473 (3)0.66985 (10)0.0753 (9)
H840.38561.18750.68020.090*
Cl10.35681 (11)0.88550 (7)0.47556 (2)0.0782 (2)
Cl20.58352 (11)0.80880 (8)0.60476 (2)0.0822 (3)
Cl30.04078 (11)0.14664 (8)0.45379 (2)0.0864 (3)
Cl40.21831 (12)0.09422 (7)0.58701 (2)0.0857 (3)
Cl50.22283 (13)0.31854 (7)1.00455 (2)0.0908 (3)
Cl60.77910 (12)0.46348 (9)0.92289 (3)0.1025 (3)
Cl70.29880 (13)1.10384 (9)0.91522 (3)0.1078 (3)
Cl80.28532 (15)1.13581 (8)1.00256 (3)0.1041 (3)
O10.6782 (4)0.4692 (2)0.58123 (6)0.1233 (11)
O20.1903 (4)0.4530 (2)0.58475 (6)0.1252 (11)
O30.5371 (3)0.78191 (18)0.92017 (5)0.0762 (6)
O40.1358 (3)0.79051 (19)0.89152 (6)0.0979 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0576 (17)0.0577 (18)0.0498 (17)0.0040 (14)0.0044 (14)0.0024 (14)
C20.106 (3)0.067 (2)0.0499 (18)0.0007 (18)0.0107 (17)0.0125 (16)
C30.130 (3)0.0578 (19)0.055 (2)0.0131 (19)0.0115 (19)0.0109 (16)
C40.0689 (19)0.065 (2)0.0430 (17)0.0082 (15)0.0037 (14)0.0047 (15)
C50.0500 (16)0.0671 (19)0.0463 (16)0.0092 (14)0.0059 (13)0.0077 (15)
C60.0584 (18)0.0527 (17)0.0615 (19)0.0134 (14)0.0100 (15)0.0074 (15)
C70.092 (2)0.078 (2)0.0538 (19)0.0232 (19)0.0014 (17)0.0025 (17)
C80.070 (2)0.071 (2)0.0507 (18)0.0136 (16)0.0034 (15)0.0040 (15)
C90.0593 (18)0.0650 (18)0.0562 (19)0.0086 (15)0.0045 (15)0.0043 (15)
C100.0435 (15)0.0525 (16)0.0505 (17)0.0013 (12)0.0086 (13)0.0028 (13)
C110.0548 (17)0.0573 (17)0.0569 (18)0.0187 (14)0.0041 (14)0.0067 (14)
C120.0548 (17)0.0509 (16)0.0521 (18)0.0104 (13)0.0083 (14)0.0014 (13)
C130.0385 (14)0.0422 (14)0.0492 (16)0.0036 (11)0.0106 (12)0.0049 (12)
C140.0557 (16)0.0400 (15)0.0536 (17)0.0038 (12)0.0108 (13)0.0087 (13)
C150.0618 (18)0.0416 (15)0.0527 (18)0.0008 (13)0.0143 (14)0.0015 (13)
C160.0431 (15)0.0412 (14)0.0509 (16)0.0039 (12)0.0113 (13)0.0054 (12)
C170.0611 (18)0.0580 (17)0.0558 (19)0.0067 (14)0.0062 (15)0.0032 (14)
C180.079 (2)0.070 (2)0.054 (2)0.0032 (17)0.0095 (17)0.0036 (16)
C190.074 (2)0.083 (2)0.0463 (17)0.0148 (18)0.0043 (16)0.0097 (17)
C200.067 (2)0.078 (2)0.063 (2)0.0051 (17)0.0012 (17)0.0197 (17)
C210.0595 (18)0.0577 (17)0.0568 (19)0.0069 (14)0.0073 (15)0.0083 (14)
C220.0595 (18)0.082 (2)0.0472 (18)0.0130 (16)0.0053 (14)0.0039 (16)
C230.139 (3)0.081 (3)0.052 (2)0.006 (2)0.011 (2)0.0127 (18)
C240.165 (4)0.065 (2)0.062 (2)0.008 (2)0.009 (2)0.0031 (18)
C250.076 (2)0.066 (2)0.0480 (18)0.0185 (16)0.0031 (15)0.0008 (15)
C260.0502 (17)0.071 (2)0.0458 (16)0.0113 (14)0.0010 (13)0.0002 (14)
C270.0559 (18)0.0693 (19)0.0548 (18)0.0019 (14)0.0018 (14)0.0076 (16)
C280.095 (2)0.070 (2)0.061 (2)0.0267 (18)0.0004 (17)0.0055 (17)
C290.071 (2)0.0609 (18)0.0543 (18)0.0153 (15)0.0018 (15)0.0088 (15)
C300.0582 (18)0.0540 (17)0.0610 (19)0.0094 (13)0.0014 (14)0.0065 (15)
C310.0423 (15)0.0490 (16)0.0535 (17)0.0010 (12)0.0068 (12)0.0095 (13)
C320.0593 (18)0.0506 (16)0.0579 (19)0.0123 (13)0.0060 (14)0.0107 (14)
C330.0579 (17)0.0516 (17)0.0531 (18)0.0063 (13)0.0104 (14)0.0166 (14)
C340.0393 (14)0.0437 (15)0.0518 (16)0.0048 (12)0.0123 (12)0.0087 (13)
C350.0561 (17)0.0373 (14)0.0606 (18)0.0020 (12)0.0111 (14)0.0066 (13)
C360.0609 (18)0.0472 (16)0.0524 (18)0.0014 (13)0.0115 (14)0.0134 (13)
C370.0470 (16)0.0425 (15)0.0540 (17)0.0064 (12)0.0123 (13)0.0064 (13)
C380.0656 (19)0.0605 (18)0.0548 (19)0.0038 (14)0.0138 (15)0.0081 (15)
C390.086 (2)0.074 (2)0.055 (2)0.0036 (19)0.0174 (17)0.0079 (16)
C400.079 (2)0.076 (2)0.056 (2)0.0115 (18)0.0045 (17)0.0076 (17)
C410.064 (2)0.067 (2)0.071 (2)0.0013 (15)0.0030 (17)0.0054 (17)
C420.0595 (18)0.0562 (17)0.0604 (19)0.0002 (14)0.0121 (15)0.0056 (15)
C430.077 (2)0.062 (2)0.0493 (17)0.0197 (17)0.0141 (16)0.0013 (14)
C440.0636 (19)0.073 (2)0.0599 (19)0.0166 (17)0.0026 (15)0.0028 (16)
C450.0622 (19)0.0564 (17)0.0564 (18)0.0063 (14)0.0012 (15)0.0013 (14)
C460.0583 (18)0.0585 (18)0.0446 (16)0.0138 (15)0.0025 (14)0.0091 (13)
C470.0602 (18)0.068 (2)0.0584 (18)0.0024 (16)0.0081 (15)0.0127 (16)
C480.085 (2)0.0536 (18)0.062 (2)0.0007 (17)0.0200 (18)0.0027 (16)
C490.0553 (18)0.0629 (19)0.0601 (19)0.0151 (15)0.0040 (14)0.0095 (16)
C500.0653 (19)0.0618 (18)0.0596 (19)0.0149 (15)0.0014 (15)0.0061 (15)
C510.0556 (17)0.0607 (18)0.0611 (19)0.0110 (14)0.0083 (15)0.0050 (15)
C520.0456 (15)0.0534 (16)0.0507 (17)0.0056 (13)0.0065 (13)0.0008 (14)
C530.0599 (18)0.0556 (17)0.0598 (19)0.0115 (14)0.0081 (15)0.0066 (15)
C540.0553 (17)0.0489 (16)0.0640 (19)0.0126 (13)0.0073 (14)0.0056 (14)
C550.0383 (14)0.0471 (16)0.0558 (17)0.0007 (12)0.0098 (12)0.0056 (13)
C560.0527 (16)0.0475 (16)0.0600 (19)0.0042 (13)0.0072 (14)0.0032 (14)
C570.0532 (17)0.0485 (16)0.0614 (19)0.0110 (13)0.0042 (14)0.0059 (14)
C580.0427 (15)0.0555 (17)0.0545 (17)0.0057 (13)0.0098 (13)0.0050 (14)
C590.0543 (18)0.0700 (19)0.062 (2)0.0043 (15)0.0059 (15)0.0079 (16)
C600.064 (2)0.092 (2)0.070 (2)0.0015 (18)0.0012 (18)0.021 (2)
C610.067 (2)0.117 (3)0.055 (2)0.012 (2)0.0060 (18)0.014 (2)
C620.077 (2)0.109 (3)0.060 (2)0.003 (2)0.0172 (18)0.0102 (19)
C630.0613 (19)0.081 (2)0.059 (2)0.0067 (16)0.0106 (16)0.0027 (17)
C640.096 (3)0.063 (2)0.0572 (19)0.0030 (19)0.0168 (18)0.0113 (16)
C650.080 (2)0.073 (2)0.075 (2)0.0187 (19)0.0123 (19)0.0172 (19)
C660.088 (2)0.0579 (19)0.070 (2)0.0233 (18)0.0218 (19)0.0078 (17)
C670.071 (2)0.0520 (17)0.0627 (19)0.0183 (15)0.0217 (16)0.0129 (15)
C680.079 (2)0.0606 (19)0.070 (2)0.0246 (17)0.0233 (18)0.0112 (17)
C690.107 (3)0.0561 (19)0.069 (2)0.0205 (19)0.030 (2)0.0052 (17)
C700.076 (2)0.056 (2)0.080 (2)0.0119 (17)0.0253 (18)0.0037 (18)
C710.076 (2)0.0505 (17)0.077 (2)0.0079 (16)0.0219 (18)0.0039 (17)
C720.0581 (19)0.0539 (18)0.093 (3)0.0006 (15)0.0279 (18)0.0052 (18)
C730.0465 (16)0.0535 (18)0.075 (2)0.0024 (14)0.0192 (15)0.0064 (16)
C740.0588 (19)0.0461 (17)0.094 (3)0.0068 (14)0.0251 (18)0.0087 (17)
C750.0537 (18)0.0550 (19)0.085 (2)0.0080 (14)0.0174 (17)0.0197 (17)
C760.0386 (15)0.0515 (17)0.078 (2)0.0043 (13)0.0202 (14)0.0172 (16)
C770.0585 (18)0.0486 (17)0.077 (2)0.0060 (14)0.0114 (16)0.0042 (16)
C780.0580 (18)0.0500 (18)0.084 (2)0.0093 (14)0.0135 (17)0.0128 (16)
C790.0469 (17)0.0583 (18)0.074 (2)0.0010 (14)0.0197 (15)0.0180 (16)
C800.058 (2)0.0637 (19)0.092 (3)0.0018 (16)0.0141 (18)0.0252 (18)
C810.070 (2)0.094 (3)0.089 (3)0.007 (2)0.004 (2)0.037 (2)
C820.072 (2)0.114 (3)0.069 (2)0.023 (2)0.012 (2)0.026 (2)
C830.077 (2)0.102 (3)0.081 (3)0.002 (2)0.025 (2)0.002 (2)
C840.059 (2)0.086 (2)0.081 (2)0.0126 (17)0.0162 (18)0.0090 (19)
Cl10.0887 (6)0.0744 (5)0.0680 (5)0.0050 (4)0.0059 (4)0.0166 (4)
Cl20.0871 (6)0.1052 (6)0.0594 (5)0.0335 (5)0.0017 (4)0.0208 (4)
Cl30.0873 (6)0.1226 (7)0.0516 (5)0.0152 (5)0.0028 (4)0.0166 (5)
Cl40.1059 (7)0.0890 (6)0.0611 (5)0.0160 (5)0.0179 (5)0.0028 (4)
Cl50.1198 (7)0.0765 (6)0.0782 (6)0.0405 (5)0.0177 (5)0.0176 (4)
Cl60.0767 (6)0.1108 (7)0.1127 (8)0.0194 (5)0.0124 (5)0.0011 (6)
Cl70.1019 (7)0.1111 (7)0.1173 (8)0.0581 (6)0.0096 (6)0.0109 (6)
Cl80.1348 (9)0.0908 (6)0.0831 (6)0.0137 (6)0.0100 (6)0.0031 (5)
O10.175 (3)0.115 (2)0.0657 (15)0.079 (2)0.0086 (16)0.0019 (14)
O20.210 (3)0.0959 (19)0.0760 (17)0.083 (2)0.0051 (18)0.0078 (14)
O30.0853 (15)0.0665 (14)0.0779 (14)0.0261 (11)0.0118 (11)0.0131 (12)
O40.132 (2)0.0535 (14)0.1065 (19)0.0092 (13)0.0110 (15)0.0079 (13)
Geometric parameters (Å, º) top
C1—C61.364 (4)C43—C481.362 (4)
C1—C21.368 (4)C43—C441.370 (4)
C1—Cl11.727 (3)C43—Cl51.731 (3)
C2—C31.371 (4)C44—C451.371 (4)
C2—H20.9300C44—H440.9300
C3—C41.380 (4)C45—C461.381 (4)
C3—H30.9300C45—H450.9300
C4—C51.378 (4)C46—C471.378 (4)
C4—C71.499 (4)C46—C491.500 (4)
C5—C61.377 (4)C47—C481.382 (4)
C5—Cl21.731 (3)C47—Cl61.733 (3)
C6—H60.9300C48—H480.9300
C7—O11.216 (3)C49—O31.214 (3)
C7—C81.461 (4)C49—C501.469 (4)
C8—C91.319 (4)C50—C511.316 (4)
C8—H80.9300C50—H500.9300
C9—C101.452 (4)C51—C521.449 (4)
C9—H90.9300C51—H510.9300
C10—C111.385 (3)C52—C531.380 (4)
C10—C151.388 (3)C52—C571.395 (3)
C11—C121.370 (3)C53—C541.370 (4)
C11—H110.9300C53—H530.9300
C12—C131.386 (3)C54—C551.386 (3)
C12—H120.9300C54—H540.9300
C13—C141.392 (3)C55—C561.396 (3)
C13—C161.479 (3)C55—C581.481 (4)
C14—C151.370 (3)C56—C571.371 (3)
C14—H140.9300C56—H560.9300
C15—H150.9300C57—H570.9300
C16—C211.387 (3)C58—C631.382 (4)
C16—C171.388 (3)C58—C591.389 (4)
C17—C181.372 (4)C59—C601.374 (4)
C17—H170.9300C59—H590.9300
C18—C191.365 (4)C60—C611.364 (4)
C18—H180.9300C60—H600.9300
C19—C201.366 (4)C61—C621.367 (5)
C19—H190.9300C61—H610.9300
C20—C211.378 (4)C62—C631.381 (4)
C20—H200.9300C62—H620.9300
C21—H210.9300C63—H630.9300
C22—C231.354 (4)C64—C691.370 (4)
C22—C271.362 (4)C64—C651.373 (4)
C22—Cl31.727 (3)C64—Cl81.734 (3)
C23—C241.373 (4)C65—C661.365 (4)
C23—H230.9300C65—H650.9300
C24—C251.375 (4)C66—C671.382 (4)
C24—H240.9300C66—H660.9300
C25—C261.378 (4)C67—C681.380 (4)
C25—C281.496 (4)C67—C701.493 (4)
C26—C271.375 (4)C68—C691.374 (4)
C26—Cl41.735 (3)C68—Cl71.733 (3)
C27—H270.9300C69—H690.9300
C28—O21.215 (3)C70—O41.215 (3)
C28—C291.458 (4)C70—C711.469 (4)
C29—C301.321 (3)C71—C721.324 (4)
C29—H290.9300C71—H710.9300
C30—C311.450 (4)C72—C731.451 (4)
C30—H300.9300C72—H720.9300
C31—C321.386 (3)C73—C781.389 (4)
C31—C361.391 (3)C73—C741.389 (4)
C32—C331.367 (3)C74—C751.363 (4)
C32—H320.9300C74—H740.9300
C33—C341.388 (3)C75—C761.388 (4)
C33—H330.9300C75—H750.9300
C34—C351.399 (3)C76—C771.396 (4)
C34—C371.481 (3)C76—C791.474 (4)
C35—C361.370 (3)C77—C781.367 (4)
C35—H350.9300C77—H770.9300
C36—H360.9300C78—H780.9300
C37—C421.384 (4)C79—C841.382 (4)
C37—C381.390 (3)C79—C801.394 (4)
C38—C391.370 (4)C80—C811.366 (4)
C38—H380.9300C80—H800.9300
C39—C401.372 (4)C81—C821.360 (5)
C39—H390.9300C81—H810.9300
C40—C411.368 (4)C82—C831.374 (5)
C40—H400.9300C82—H820.9300
C41—C421.379 (4)C83—C841.376 (4)
C41—H410.9300C83—H830.9300
C42—H420.9300C84—H840.9300
C6—C1—C2121.2 (3)C48—C43—C44121.2 (3)
C6—C1—Cl1119.7 (2)C48—C43—Cl5119.0 (3)
C2—C1—Cl1119.0 (2)C44—C43—Cl5119.8 (3)
C1—C2—C3118.3 (3)C43—C44—C45119.5 (3)
C1—C2—H2120.9C43—C44—H44120.3
C3—C2—H2120.9C45—C44—H44120.3
C2—C3—C4122.6 (3)C44—C45—C46121.1 (3)
C2—C3—H3118.7C44—C45—H45119.4
C4—C3—H3118.7C46—C45—H45119.4
C5—C4—C3117.2 (3)C47—C46—C45117.8 (3)
C5—C4—C7125.5 (3)C47—C46—C49125.1 (3)
C3—C4—C7117.2 (3)C45—C46—C49117.1 (3)
C6—C5—C4121.3 (3)C46—C47—C48121.8 (3)
C6—C5—Cl2116.5 (2)C46—C47—Cl6120.8 (2)
C4—C5—Cl2122.2 (2)C48—C47—Cl6117.4 (2)
C1—C6—C5119.4 (3)C43—C48—C47118.6 (3)
C1—C6—H6120.3C43—C48—H48120.7
C5—C6—H6120.3C47—C48—H48120.7
O1—C7—C8122.1 (3)O3—C49—C50122.3 (3)
O1—C7—C4118.9 (3)O3—C49—C46118.6 (3)
C8—C7—C4119.0 (3)C50—C49—C46119.0 (3)
C9—C8—C7122.7 (3)C51—C50—C49121.4 (3)
C9—C8—H8118.6C51—C50—H50119.3
C7—C8—H8118.6C49—C50—H50119.3
C8—C9—C10126.9 (3)C50—C51—C52129.2 (3)
C8—C9—H9116.5C50—C51—H51115.4
C10—C9—H9116.5C52—C51—H51115.4
C11—C10—C15117.0 (2)C53—C52—C57117.1 (2)
C11—C10—C9120.0 (2)C53—C52—C51118.9 (2)
C15—C10—C9123.0 (2)C57—C52—C51123.9 (2)
C12—C11—C10121.7 (2)C54—C53—C52121.7 (3)
C12—C11—H11119.2C54—C53—H53119.2
C10—C11—H11119.2C52—C53—H53119.2
C11—C12—C13121.7 (2)C53—C54—C55121.8 (3)
C11—C12—H12119.2C53—C54—H54119.1
C13—C12—H12119.2C55—C54—H54119.1
C12—C13—C14116.5 (2)C54—C55—C56116.6 (2)
C12—C13—C16121.1 (2)C54—C55—C58121.2 (2)
C14—C13—C16122.4 (2)C56—C55—C58122.2 (2)
C15—C14—C13121.9 (2)C57—C56—C55121.6 (3)
C15—C14—H14119.0C57—C56—H56119.2
C13—C14—H14119.0C55—C56—H56119.2
C14—C15—C10121.2 (2)C56—C57—C52121.2 (2)
C14—C15—H15119.4C56—C57—H57119.4
C10—C15—H15119.4C52—C57—H57119.4
C21—C16—C17116.5 (2)C63—C58—C59117.2 (3)
C21—C16—C13121.9 (2)C63—C58—C55121.8 (3)
C17—C16—C13121.5 (2)C59—C58—C55121.0 (3)
C18—C17—C16121.7 (3)C60—C59—C58121.3 (3)
C18—C17—H17119.2C60—C59—H59119.3
C16—C17—H17119.2C58—C59—H59119.3
C19—C18—C17120.6 (3)C61—C60—C59120.5 (3)
C19—C18—H18119.7C61—C60—H60119.8
C17—C18—H18119.7C59—C60—H60119.8
C18—C19—C20119.1 (3)C60—C61—C62119.4 (3)
C18—C19—H19120.4C60—C61—H61120.3
C20—C19—H19120.4C62—C61—H61120.3
C19—C20—C21120.5 (3)C61—C62—C63120.4 (3)
C19—C20—H20119.8C61—C62—H62119.8
C21—C20—H20119.8C63—C62—H62119.8
C20—C21—C16121.5 (3)C62—C63—C58121.2 (3)
C20—C21—H21119.2C62—C63—H63119.4
C16—C21—H21119.2C58—C63—H63119.4
C23—C22—C27120.9 (3)C69—C64—C65120.9 (3)
C23—C22—Cl3119.6 (3)C69—C64—Cl8119.4 (3)
C27—C22—Cl3119.5 (3)C65—C64—Cl8119.7 (3)
C22—C23—C24118.6 (3)C66—C65—C64118.6 (3)
C22—C23—H23120.7C66—C65—H65120.7
C24—C23—H23120.7C64—C65—H65120.7
C23—C24—C25122.9 (3)C65—C66—C67122.8 (3)
C23—C24—H24118.6C65—C66—H66118.6
C25—C24—H24118.6C67—C66—H66118.6
C24—C25—C26116.4 (3)C68—C67—C66116.7 (3)
C24—C25—C28116.7 (3)C68—C67—C70126.5 (3)
C26—C25—C28126.9 (3)C66—C67—C70116.8 (3)
C27—C26—C25121.8 (3)C69—C68—C67122.0 (3)
C27—C26—Cl4116.5 (2)C69—C68—Cl7117.4 (2)
C25—C26—Cl4121.7 (2)C67—C68—Cl7120.5 (3)
C22—C27—C26119.4 (3)C64—C69—C68119.1 (3)
C22—C27—H27120.3C64—C69—H69120.5
C26—C27—H27120.3C68—C69—H69120.5
O2—C28—C29121.3 (3)O4—C70—C71121.3 (3)
O2—C28—C25118.6 (3)O4—C70—C67118.4 (3)
C29—C28—C25120.0 (3)C71—C70—C67120.0 (3)
C30—C29—C28122.4 (3)C72—C71—C70121.1 (3)
C30—C29—H29118.8C72—C71—H71119.5
C28—C29—H29118.8C70—C71—H71119.5
C29—C30—C31127.8 (3)C71—C72—C73129.1 (3)
C29—C30—H30116.1C71—C72—H72115.5
C31—C30—H30116.1C73—C72—H72115.5
C32—C31—C36116.7 (2)C78—C73—C74116.9 (3)
C32—C31—C30119.9 (2)C78—C73—C72124.2 (3)
C36—C31—C30123.4 (2)C74—C73—C72118.9 (3)
C33—C32—C31122.1 (2)C75—C74—C73121.7 (3)
C33—C32—H32118.9C75—C74—H74119.1
C31—C32—H32118.9C73—C74—H74119.1
C32—C33—C34121.5 (2)C74—C75—C76121.8 (3)
C32—C33—H33119.2C74—C75—H75119.1
C34—C33—H33119.2C76—C75—H75119.1
C33—C34—C35116.5 (2)C75—C76—C77116.3 (3)
C33—C34—C37121.4 (2)C75—C76—C79121.9 (3)
C35—C34—C37122.1 (2)C77—C76—C79121.8 (3)
C36—C35—C34121.8 (2)C78—C77—C76121.9 (3)
C36—C35—H35119.1C78—C77—H77119.0
C34—C35—H35119.1C76—C77—H77119.0
C35—C36—C31121.3 (2)C77—C78—C73121.3 (3)
C35—C36—H36119.3C77—C78—H78119.4
C31—C36—H36119.3C73—C78—H78119.4
C42—C37—C38117.5 (3)C84—C79—C80116.9 (3)
C42—C37—C34121.3 (2)C84—C79—C76122.0 (3)
C38—C37—C34121.1 (2)C80—C79—C76121.1 (3)
C39—C38—C37121.2 (3)C81—C80—C79121.4 (3)
C39—C38—H38119.4C81—C80—H80119.3
C37—C38—H38119.4C79—C80—H80119.3
C38—C39—C40120.6 (3)C82—C81—C80120.5 (3)
C38—C39—H39119.7C82—C81—H81119.7
C40—C39—H39119.7C80—C81—H81119.7
C41—C40—C39119.1 (3)C81—C82—C83119.7 (4)
C41—C40—H40120.5C81—C82—H82120.1
C39—C40—H40120.5C83—C82—H82120.1
C40—C41—C42120.7 (3)C82—C83—C84119.8 (4)
C40—C41—H41119.7C82—C83—H83120.1
C42—C41—H41119.7C84—C83—H83120.1
C41—C42—C37120.9 (3)C83—C84—C79121.6 (3)
C41—C42—H42119.6C83—C84—H84119.2
C37—C42—H42119.6C79—C84—H84119.2
Dihedral angles (°) within biphenyl groups and between biphenyl and dichlorophenyl groups. top
MoleculeDihedral angle (biphenyl)Dihedral angle (biphenyl/dichlorophenyl)
a17.67 (7)46.27 (7)
b24.52 (8)47.25 (8)
c18.91 (7)66.95 (8)
d24.17 (9)60.56 (8)
Notes: for the calculation of the dihedral angle between the biphenyl group and the dichlororphenyl group, a least-squares plane for all atoms of the biphenyl group was calculated. Molecule a contains atoms from Cl1 to H21, molecule b contains atoms from Cl3 to H42, molecule c contains atoms from Cl5 to H63 and molecule d contains atoms from Cl7 to H84.
 

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